Oxalyl chloride → HCID 11041567, compound

HRID 2165942Notes

Reaction equation

HRID 2165942 reaction equation
[CH3:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>C1C=CC=CC=1>[CH3:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4]([Cl:16])=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 13191833(R)-(+)-3,7-dimethyloctanoic acid

Product 1

HCID 11041567HCID 11041567, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 11.37 g (66.1 mmoles) of (R)-(+)-3,7dimethyloctanoic acid in 50 ml of benzene was stirred while 10 ml (114.6 mmoles) of oxalyl chloride was added. The solution was stirred and refluxed overnight then concentrated in vacuo giving 12.03 g (95.6 %) of (R)-(+) -3,7-dimethyloctanoyl chloride as an oil. An 8.2 g (43.0 mmoles) sample of this material in 10 ml of dichloromethane was added to a stirred solution of 6.2 (43.0 mmoles) of Meldrum's Acid and 8.68 ml of pyridine in 40 ml of dichloromethane, at 0° C. The resulting solution was stirred overnight then treated with cold 3N agueous HCl. The organic phase was separated and the agueous phase was extracted with dichloromethane. The dichloromethane extracts were combined dried (Na2SO4), and concentrated in vacuo giving 12.1 g of crude product. This material was dissolved in 100 ml of methanol and the solution was refluxed for 4 hr then cooled and concentrated in vacuo. The residue was chromatographed on silica gel giving (R)-5,9-dimethyl-3-oxodecanoic acid methyl ester as an oil, eluted with pet. ether - ether mixtures.

Workup

  1. additionwas added
  2. temperaturerefluxed overnight
  3. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-6bf3525a7731402eb80e2227beacbe3d
Source dataset
uspto-grants-1990_07
Patent number
US04942249

Reaction notes

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